


Handsome Hobo

by relenafanel, Swing Set in December (swing_set13)



Category: Teen Wolf (TV)
Genre: Coffee, Comedy, Derek doesn't help matters through his behaviour, Derek is a history professor, Homelessness, M/M, Mistaken Identity, Neighbors, but Stiles mistakes him for a hobo
Language: English
Status: Completed
Published: 2014-04-19
Updated: 2014-04-19
Packaged: 2018-01-20 01:28:27
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 8,853
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1491730
Author URL: https://archiveofourown.org/users/relenafanel/pseuds/relenafanel, https://archiveofourown.org/users/swing_set13/pseuds/Swing%20Set%20in%20December
Summary: <blockquote class="userstuff">
              <p>Derek should probably stop rummaging through garbage if he doesn't want people to assume he's homeless.</p>
            </blockquote>





	Handsome Hobo

**Author's Note:**

> Thank you to everyone who waited patiently for this fic to be posted on AO3. I know a lot of you have been following it since its inception on AO3 and know how tangled the web we weaved truly was. 
> 
> <3 [relenafanel](http://relenafanel.tumblr.com/) and [swingsetindecember](http://swingsetindecember.tumblr.com/)
> 
> The [wonderful handsome hobo art](http://reallyyeahokay.tumblr.com/post/60098211304/relenafanel-and-swingsetindecember-consumed-my) by [reallyyeahokay](http://reallyyeahokay.tumblr.com/) was inspired by the fic. Same goes with the [beautiful handsome hobo art](http://belayday.tumblr.com/post/60677404214/relenafanel-and-swingsetindecembers-not-hobo) and [gorgeous handsome hobo art](http://belayday.tumblr.com/post/60801460505/bringing-a-whole-new-meaning-to-the-term-tube) by [belayday](http://belayday.tumblr.com/). Check it out and reblog it on tumblr.

Derek’s trying to warm his fingers against the frigid morning air. He blearily makes a note to dig out his winter gear from storage before the temperature drops any lower.  For now, he has piecemeal layers on, each added to his autumn attire as it got chillier out.  And it works.   He’s not freezing, he just needs gloves so he can stop pulling his sweater down over his hands.  Last week, he wore a thumb hole right through, and it was the best, most Eureka part of his week.

Thumb holes, who knew?

His jaw cracks in a big yawn and he regrets taking over Deaton’s morning lectures this semester. There’s no way he’ll ever wake up early enough to shave if he has to make it across the city before the sun is even up. Maybe he’ll just let his beard grow out for the next few months. Just give into academia as it were. He sits against the apartment complex’s stoop as the sun fights to emerge and lets his eyes droop. It doesn’t matter if he nods off, he tells himself with the kind of certainty of the exhausted, he’ll hear the bus coming anyway. It’s just his luck he left his iPod under a pile of unread journals in his loft.  Music always helps him feel more alive.

There’s an awkward cough that has him cracking open his right eye to see a handsome plaid-shirt-wearing hipster worrying his lip between his teeth. 

Derek just sighs because he’s not blocking the stairs at all but he shifts more into the cool concrete of the building to let the guy pass. 

The guy shoots him another look before walking down the street. 

If Derek had the energy, he’d scowl, but he’d already expended it shifting his body weight to get out of the guy’s way.  He’s not really sure what the point of all that was, and isn’t sure he cares.

Derek smothers another yawn behind the arm of his sleeve and considers whether the staff room will have a fresh pot of coffee or not.  Half the time, the heating pad is turned on and no one thought to start another pot, allowing that last quarter of an inch to burn.

No one is worse or feels that particular brand of entitlement towards caffeine than professors and PhD candidates who have to deal with undergrads. Especially before 8 AM.  Derek would have better luck waking up fifteen minutes earlier and making his own coffee, but if he had that kind of commitment, he wouldn’t be well on his way towards growing a beard, now would he?

***

By the time Stiles gets back to the front stoop of his building, the guy is gone and Stiles is left holding a steaming take out mug of coffee from the McDonalds at the corner.  There’s a Starbucks across the street from it, but Stiles can’t afford that for himself, and he’d be tempted to splurge for someone who doesn’t look like they have an easy life, but the guy looks like he needs an actual meal more than a venti of steamed milk.

Stiles is a bit disappointed that he didn’t get the chance to give the guy… the really handsome hobo, and the alliteration of it is simultaneously driving Stiles nuts for somehow making light of what isn’t a light issue and MAKING HIS DAY… the coffee.  He takes a moment to glance down the alley between his building and the next, because about a week after he moved into the building he had first spotted Handsome Hobo as he rummaged through the trash.

But no such luck.  The man seems to have disappeared.

"Damn," Stiles mutters to himself as he takes a sip of the coffee, and he can say this with certainty… it is pleasantly hot.  Drinking it feels a bit like taking something from someone who needs it more, or like kicking puppies, but there’s not much he can do if Handsome Hobo just disappeared.  Is there?

He thinks about it for a moment.  He does have some yarn in a nice blood orange colour, and the thought makes him snicker a bit to himself because now he’s thinking about that Project Runway quote.

Not that he watches Project Runway or anything.

Often.

He did pick up tips for how to embroider leather from it though.  And he’s pretty sure that the yarn he has is enough to make a pair of mittens.  The Handsome Hobo had been rubbing his fingers together like he was cold, and Stiles has no idea how to knit individual fingers, so mittens are perfect! They’ll keep Handsome Hobo with all his digits over the winter, anyway.

Probably.

***

Derek swipes his gold card at the Starbucks across the street and waits for Danny to make his venti vanilla latte. He’s running a bit early this morning and will actually have caffeine that doesn’t taste like the battery acid that drips from the history departments’ office lounge before he takes on a lecture hall of half asleep 4th years. 

"Nice gloves, Miguel,” comments Danny congenially before handing him is order. Baristas always have a twisted sense of humor. 

The mittens the Handsome Hipster gave him are on his hands, Derek doesn’t remember putting them on but then again, Derek doesn’t remember shaving again this morning. They’re surprisingly warm. 

***

Stiles doesn’t see the Handsome Hobo for days.  He thought he might have seen him once coming out of the Starbucks, but it turned out to just be a well-groomed look-alike, all clean shaven and wearing pants that weren’t frayed.  So, just another suit that lived in the neighbourhood due to gentrification. 

A very handsome suit, but Stiles’ heart belonged to another now, and besides he’d only gotten a quick glance.

Stiles doesn’t have much disposable income.  He’s sharing a one-bedroom plus den with Scott and tries to pretend that his double bed doesn’t take up the entire room, but he feels like it’s time to get aggressively proactive when he comes across Handsome Hobo napping on a bench in the small monument park across the street as he cuts through on a path.  It’s his quickest way home, even though half of his neighbours are real jerks about cleaning up after their pets.  Even when he’s watching where he steps, cutting through the park still cuts off about five minutes of walking time.  

He’s not sure what he’s seeing when he comes across Handsome Hobo.  At first he thinks it’s just some discarded clothing on the bench - someone’s jacket or something.  Then it takes shape and Stiles thinks ‘oh boy, a dead body’ with a combination of dread and curiosity.  

When the person moves, exposing his face, Stiles recognises him instantly. The man is wearing the mittens Stiles gave him, and his fingers are curled against his nose, keeping it warm in the cool autumn air, and Stiles is just… his heart aches, ok? 

"Hey," Stiles says, carefully placing his hand on Handsome Hobo’s shoulder.  He’s heard the stories from his dad, and has seen the episodes of crime shows, and knows the statistics of how many homeless people are war veterans, especially in today’s society where Stiles feels like he’s $30 in the bank from not being able to make rent himself.  He’s careful with the way he touches the sleeping stranger, thinks it’s probably a terrible idea to startle anyone whose entire possessions are on their back.

The guy sleepily looks up at him.

"Is there someone who can help?" Stiles asks.

"My sister," he says, blinking in confusion as he takes in his surroundings.  Stiles can feel the chill in the air and it hasn’t gotten bad yet, but he knows stats on hypothermia.  "I’ve called her five times," the guy says, sitting up now.

Stiles just breaks.  Suddenly furious at this faceless sister who would just… just… leave him like this.

"It’s not much," he says, pulling out the $30 from his wallet and pressing it into the guy’s hand and walking away quickly, before Handsome Hobo, who strikes Stiles as being very willful and proud, can turn him down.

***

Derek is still holding the crumpled bills in his hand when Laura pulls up in her Camaro, revving the engine. 

"Hey loser! Get in!" she shouts merrily. "I know I’m a little late but what’s with the kicked puppy look, did Deaton say you had to shave your beard for the chair of the department again?"

"That hipster gave me thirty dollars," he says with befuddlement.

"You mean the cutie that just walked by? Isn’t he from your building?"

"Second floor," Derek gets into the passenger seat. "And you were more than a little late," he says hotly, forgetting about the money. "Five hours, Laura. I could have been researching."

"So I got you outside. Help with that pale complexion Mom worries about," Laura says dismissively. "Saves her from nagging Cora about her new tattoo."

"Tattoo!" Derek sputters. The Handsome Hipster fading from his mind, as does the fact Laura kept his keys hostage for five hours.  He should have known better than to hand her the whole set.

The thirty dollars goes in his pocket, and becomes one with all the cash Derek finds upon emptying his pants on laundry day.  From there, it gets shoved in his wallet, and he doesn’t even remember where the extra thirty came from when he’s splurging on a cake pop for lunch.

The Handsome Hipster with the dark framed glasses and the ridiculous eyes doesn’t even enter his mind until the next week when he overhears him arguing with Scott McCall, the guy who organizes the building’s compost, about not making rent. 

He crams sixty dollars into the Handsome Hipster’s hand before walking briskly away the next morning. The guy looks like he’s been living off ramen, and Derek’s still confused as to why he was handed the thirty dollars in the first place.

***

UHM Stiles thinks really hard, eyes crossing in confusion as he’s left holding double. DOUBLE. the amount he had given Handsome Hobo the week before.  UHM.  He’s having a major moral dilemma here.  On the one hand, there’s not enough room in the tiny space beneath the stairs he secretly suspects Handsome Hobo sleeps in most nights for Stiles and Scott to crawl in there as well (which is what would happen if Stiles DOESN’T use this money towards rent), but at the same time can he take money from someone who doesn’t have money to spare?

"Dude," he says to Scott, bursting into the apartment with his hand closed into a protective fist around the cash. "DUDE I HAVE MY VERY OWN PRISONER’S DILEMMA HERE," he says, waving the cash.

"Did you rob a bank?" Scott asks.  "Take it out of the ATM behind someone’s back?  Cameras pick that stuff up, Stiles!"

"…no." Stiles squints.  

"Then I don’t see how you’d be arrested."

"I wouldn’t be… you took a philosophy course first year! NO! The Handsome Hobo gave me money. He gave me money, Scott. What do I do?  The man is homeless, Scott.  Homeless. And he just gave me money.  Do you think maybe we should let him sleep on the couch?"

"Who?"

"THE HOMELESS GUY WHO SITS AT THE BOTTOM OF THE STEPS WITH HIS COFFEE CUP SCOTT. SOMEONE DROPPED CASH INTO IT THE OTHER DAY. YOU WERE THERE.”

"You mean Derek?" Scott asks, looking so unimpressed he goes back to shoving his hands in a pile of garbage, like his compost pile now seems a preferable option to the conversation he’s having.  When Scott had suggested the building get a compost, he hadn’t expected people to just start shoving their egg shells and other organic-ish garbage at him.  Stiles had laughed for days.  "While that was hilarious, don’t you think you’re taking the joke a little too far by CALLING him homeless?"

Stiles gives Scott a squirrelly look. “Who?”

Scott returns the look with even more of a judgemental frown. A Melissa McCall 2.0 look. 

"I don’t know who you are talking about," declares Stiles. 

"Who are you talking about?” asks Scott. “And stop waving money around. Go pay Finstock before he has an aneurysm and shuts off our hot water.”

"I-," Stiles begins. "I hope you can sleep tonight. Because I won’t," Stiles hisses before leaving the apartment. Scott’s ignoring him in guise of organizing the garbage.

Who can compost at a time like this?

He has to find Handsome Hobo and make things right.

Finstock has an eerie sixth sense about rent because he corners him before he can get out to the stoop and misses the Handsome Hobo by seconds as he gets on the 140 bus. 

Stiles has to make this up somehow. 

***

True to his word, Stiles doesn’t sleep that night for worry.  What if it’s freezing, and Handsome Hobo gave Stiles his last $60 and doesn’t have enough for the shelter, and in the morning Stiles wakes up and finds Handsome Hobo dead on the stoop like the Little Match Girl.  That story made Stiles cry as a child.  He isn’t prepared to live it in the role of the villainous people who didn’t open their doors and their hearts.  He’s trying! His heart is very much open!

He stumbles out of bed after midnight and grabs the extra sheets out of the closet.  He makes up the futon he and Scott use to rest their backs against while gaming from the floor and, feeling guilty, goes out into the night in search of Handsome Hobo.

Handsome Hobo isn’t sleeping in the hallway downstairs beneath the mailboxes.

He isn’t sleeping in the crawl space beneath the stairs. Stiles knows this because he stuck his head under there while saying “hello?” in his friendliest tone, only to get attacked by an angry cat.

Or raccoon.

He’s up on his shots, he’s not sure the distinction matters much unless he gets some kind of necrosis from it, and then EW.

Handsome Hobo isn’t around the dumpster, either.   He’s not IN the dumpster.

(what? he imagines it’s warm in there what with the gases of decomp and the four walls and the lid)

But no Handsome Hobo.  Stiles feels really guilty about this.  He tries to stay up waiting on the step and everything, and makes it for about half an hour, miserable, until his ass turns numb and he’s forced to go back inside, which just MAKES HIM FEEL WORSE ABOUT IT, OK?

It doesn’t make him feel any better to know that if Handsome Hobo dies tonight because of the cold, it won’t be on his doorstep.  If anything that makes him feel worse, because he tried, and whatever anonymous doorstep Handsome Hobo dies on won’t try.

They just won’t try at all, because no one cares in this city.  No one cares in this country.

People suck.

So the next time he sees Handsome Hobo he can’t help the overwhelming emotions he feels to know the man is still alive.  He just gives him a full body hug.  He practically glomps the man.

And he thinks, Handsome Hobo smells really good.

Not like a dumpster or like he’s sharing space with [Bert, Ralph and Melissa Raccoon ](http://en.wikipedia.org/wiki/The_Raccoons)at all.

***

Derek freezes and not from the cold. But by the full body hug he’s being privy too. He can see Isaac across the street in the Starbucks laughing and capturing it on his iPhone.

Derek really needs new friends.

But he can’t help but lean into the warmth of the Handsome Hipster who’s hugging him. For more than three Mississippi’s. A kind of personal space infringement that Derek will usually growl over has him melting. 

"You’re alive!" Handsome Hipster says. And Derek’s brow wrinkles. Half of what this guy says is always very confusing. 

"I-"

"Not that I thought you were dead but you gave me sixty dollars! Which I fully intend to pay you back - do you like muffins?"

Derek blinks again, hoping what the guy says will make more sense. “Yes?”

The Handsome Hipster practically vibrates with happiness. “Great, I make a mean lemon cranberry - if you’re free-“

"Actually, I have to go," Derek says regretfully. He wouldn’t mind talking to him more. But he’s got a class to teach soon. Isaac should be getting his coffee order instead of flirting with the barista. 

***

Handsome Hipster just shows up the next time Derek is waiting for the bus, a tupperware container of muffins in his mitten-covered hands.  Derek takes it from him, opening it up and biting into one with the enthusiasm of someone who doesn’t regularly take the time to eat in the morning because he really loves sleep.

Handsome Hipster bakes just about as well as he knits, which means the muffins are edible but… well, they’re edible.

"I have hot chocolate, too!" the guy says, and pours Derek a mug.

"Thanks," Derek answers, and it does help the muffin go down smoother.

The guy just smiles at him.  ”You can share them with the people you know from… the bus.”

Derek frowns in confusion. Why the heck would he share them with the dirty, unwashed people who typically ride the bus with him?  Some of them are his students, and they always spend the trip glaring at him like it’s his fault they’re up so early, as though he enjoys it!

(and ok, he enjoys their misery a little. Less every time he has to stare at spongebob pyjamas)

Derek has no idea why anyone would be voluntarily up this early, let alone as enthusiastically as this hipster guy in front of him... and with the time to make thermoses of hot chocolate, but… well… to each their own, Derek guesses, saluting Handsome Hipster with the muffin as he drags his tired butt onto the bus so he’ll make it to work on time.

***

"Why do you keep staring out the window?" Scott asks.

"Do you think he’s cold?"

"Who?"

"The Handsome Hobo.  I knit him a pair of mitts, and I don’t have any wool left - but I might go buy some.  I don’t want him to be cold, but I can’t think of what more I can do other than that," Stiles said morosely.  “It’s cold out, Scott, and it’s going to just keep getting colder.”

"The Handsome…"

"Hobo!"

"I…" Scott starts to say and then cuts off with a confused frown.  "I think he’s probably ok, in a shelter or something somewhere."

"I can’t make him more hot chocolate if he has my thermos!"  Stiles frets.

***

"Oh my god," the Handsome Hipster’s roommate says vaguely looking up at Derek as he holds out the thermos in front of him.

"Here. Thank him for the hot chocolate and the muffins. I shared them with my class."

"Oh my god," the roommate says again, and Derek wishes he could remember his name.  He knew it last week! It starts with an S? It’s Compost Guy! Derek always feels vaguely guilty when he sees him because as much as he loves the idea of composting, there’s only so long he can stand the scent of garbage beneath his sink before it starts driving him insane and he starts wondering if the scent is actually him.  He probably shouldn’t have retrieved those jeans from the dumpster when Cora threw them out, yelling about adult men not being allowed to wear saggy and frayed stone washed jeans.

Derek didn’t understand what half of that meant.

They were in a bag. He washed them and did the sniff test regularly, but now he’s concerned that he might smell and just not know it.

They’re really comfortable, though.

Derek’s about to turn away and head for the stairs now that he’s done his neighbourly duty in return, but something stops him.  Curiosity, maybe.  ”Do you know why he keeps giving me things?  This scarf, for instance, and the muffins, and…”

It strikes him at the last second that this might actually be a Hipster Mating Ritual and he’s being courted.

"Uh… nevermind," Derek says awkwardly.

"Oh my god," the roommate echoes a third time before shaking his head and closing the door, kind of looking stunned in a way that Derek just can’t figure out.

***

Scott’s viciously scrubbing the old cast iron Delgado pan that’s been handed down whenever the eldest moves out (he’s kind of convinced it’s the way Delgado mothers make sure their children are armed when out in the dangerous world, because that thing is heavy) when Stiles gets back from work. Scott only does dishes if he’s upset.

"Hey buddy," Stiles says cautiously, forgoing a glass when he reaches the fridge to get some milk. Scott just cleaned the two they own. It would be bad taste to dirty it.

Scott just scours the pan with more vigour.

"Are you and Allison... okay?" Stiles asks and sends a silent prayer out to whatever deity is listening that the answer is a firm decisive yes.

"Allison’s great," Scott says. "She’s finally getting a chance to teach the advanced archery class - we’re celebrating later."

"Oh, okay." Stiles sends a fist pump to the sky.

Scott rinses the pan before turning towards Stiles.

"6B came down to drop off your thermos."

"Who?"

Scott looks even more pained. And Stiles sees the empty tupperware and chipped plaid thermo in the drying rack near the sink.

"I think this joke’s gone on far enough, don’t you think?" says Scott, turning back to the pan that has a stubborn piece of grease baked into it.

"Joke?" Stiles gapes at the audacity. 6B is clearly trying to get rid of the Handsome Hobo. So what if he hangs out in the garbage behind the build? Or warms himself in the lobby? 6B has no business talking to Handsome Hobo. 6B is probably that high powered lawyer lady that drives the douchey Camaro and parks in Stiles’ space on weekends.

The next time Stiles sees her, he’s giving her a piece of his mind. A joke? Helping out the most kind hearted man ever?

Just for that, Stiles is going to make another even bigger batch of muffins. Maybe with milk? No, he just drank it all.

"I’m glad we can talk about these things," says Scott.

***

"Derek, you really need to move, the people in this building are psycho," says Laura as she uses her own - not given freely - key to get into his apartment. Derek’s spent the afternoon researching Hipster Mating Rituals. So far, he thinks he needs to get a case of PBR and some music no one’s heard of. Derek thinks maybe his medieval lyre tapes he recorded for his thesis could work.

"What?"

"A guy in a beanie just called me a capitalist pig," says Laura as she unloads the groceries she brought. "I mean, is shopping at Fresh & Easy really a crime? It’s the only place that sells the kale chips you love. God knows why.”

"It’s the only snack I know you won’t eat," says Derek, closing his browser. "And for the last time, I am not moving."

"Whatever," Laura says dismissively. "It’s bad enough I have to illegally park whenever I visit. Can’t you get me a pass?"

"And encourage you to visit more?" grumbles Derek.

Laura just laughs and throws his kale chips at his head. “Oh muffins!”

Derek manages to keep back his grin long enough for her to bite into one.  They’re a few days old now, and if anything Handsome Hipster’s baking is getting worse.  Derek knows enough about dating to never, ever mention that, though.

***

“What do you know about Hipster Mating Rituals?” Derek ends up asking Cora on the phone.  His sister is young and does things he doesn’t get, so maybe she has some insight into this.

"Hipster mating rituals? Derek, for the last time, the world is not out to seduce you."

"Not the world, just this one guy.  I think. I mean, he gave me mittens," Derek says as he walks down the steps of his building.

"Is that code for a weird sex thing? Because I don’t want to know."

"Pfft! Like Derek knows anything about weird sex," Laura interjects.  Derek, up to that point, had been blissfully unaware that this phone call is a party line with both of his sisters.  At once.  The thought makes a shiver go down his spine because both of his sisters at once.  “You haven’t seen him recently.  He doesn’t look like he’s getting any or has gotten lucky in a while.  I think he’s forgotten that sex exists.”

“How long has it been?” Cora asks.

Derek opens the front door of the building and steps out, the autumn chill making him grateful he has his knitwear on.  “Not that long... I don't think.  It won't be that hard to pick up on again.”

“If you can’t remember, it’s been too long,” Laura says.  “You’re practically a born again virgin by this point.  Should I get you a how-to manual?  A Kama Sutra for dummies? I’ll get a picture version.”

“I KNOW ABOUT SEX OK?” Derek yells and hangs up on his sisters only to see that Handsome Hipster staring at him in horror from the bottom of the steps, eyes wide.

“Oh no dude! I know things are bad, but don’t sell yourself. My dad’s a cop, maybe he knows someone who could help.”

Derek has zero idea what he’s talking about, and it must show on his face because the kid backpedals and flails a little.

"But, like, there’s nothing wrong with it if you already are, it’s just LOOK AT YOU, you’d probably make bank, so it’s a good assumption that you’re not and look, I’m just going to go before I put my foot further in my mouth. You can buzz up to 4C if it gets too cold tonight.  Please.  I worry.  The mitts are working out ok?"

Derek’s even MORE confused, because he’s not sure if he was just propositioned, or if this is about the mittens… maybe there’s a matching hat and scarf set the kid thinks he’s going to sleep in or something????

“I… have things,” Derek says, gesturing across the street towards the park.  Really, he just needs to escape.

Maybe he’ll take a nap somewhere his sisters won’t find him.  The park bench hadn’t been too bad, last time.

"Oh… well, you know, the offer for upstairs is still wide open," the Handsome Hipster says and that has Derek blushing. He’s not used to that kind of forward dating. He’d at least want coffee before sleeping with him.

***

It's not right.  

Stiles obviously knows nothing about being so down and out.  He doesn't know what he would do to survive if he was living on the streets, so he isn't judging.  He really isn't.  Who hasn't thought 'I like sex. I like money... I wonder if that would help me pay the bills'?

It's just... it makes his heart hurt even more that someone as nice as a guy who blushes at the idea of someone giving them a warm place to sleep and always seems so confused at kindness is considering using the one thing he has autonomy over to get money.  It happens.  He knows it does.

But Stiles wants Handsome Hobo to feel special, if only for a moment.  Muffins just aren't going to cut it.  Stiles decides on a nice tote bag to give the Handsome Hobo. The tote totally is cool. It’s one of those literacy awareness ones.

As a side benefit it holds the hat Stiles’ finished knitting the night before while he was obsessively watching the weather channel with Scott looking at him with concern before leaving for a date with Allison.

He's a little excited to hand both over, because they're useful presents.

...But the handsome hobo isn’t outside. Stiles briefly panics. It didn’t drop below freezing last night. BUT STILL. He has to shake his head at imagining the handsome hobo in flagrante delicto with some sleezy perv. Handsome Hobo deserves to be wooed.

Stiles hopes that at least he got a place to sleep out of it.

***

Derek takes up using the tote bag to lug his books to work, because if there’s one thing he’s noticed, it’s that his students could learn a thing or two about literacy (for fuckssakes he’s not teaching high school, it shouldn’t be difficult to understand comma splices AND MAKING SURE YOU’RE SPELLING THE TOPIC OF YOUR ESSAY RIGHT).

Every time Stiles sees it, with the hat sticking out of the top next to his travel mug, he goes a little pink, but Derek thinks that might be because winter is coming.

He says that to Stiles in somber tones and the guy just seems to vibrate in one spot and look at him like Derek is the best thing he’s ever seen, and Derek gets the reference, he does, but so does EVERYONE these days.  It doesn’t take a certain level of literacy to understand George R R Martin anymore.

(Derek really loves the tote) (no matter how awkward the kid who gave it to him was, all “it can hold your stuff. you know… STUFF. From your job. Stay safe, ok?” and Derek had just answered “ok” in a confused tone)

The next time Stiles sees him, he seems more subdued. “Winter is coming,” he says as somberly as the characters from the books, and hands over a scarf.

***

Suddenly, Derek know exactly what to give the Handsome Hipster in return for all his gifts.  He’s been over-thinking it for days, feeling snug in the scarf and wanting to give something of himself back.  It gets caught a bit in his facial hair, but whatever.  It might not be perfect, it might not be something someone could ever sell on Etsy, but it was perfect to Derek.

***

The CD is semi-professionally published, in that way CDs from small recording companies always look this side of someone burning it on their desktop and then sticking on sticker printed from their printer. It's obvious that at some point in time someone had been proud enough of their new printer, or whatever, that they'd taken the time to create a label for it, but it's the most confusing label Stiles has ever seen.

D. Hale. The Saxon Lyre. Independent Study, Autumn 2005.

"Thanks," Stiles says with a smile, turning the CD case over in his hands.  It's clean and in really good condition, so Stiles doesn't mind tucking it into his bag.  He would, anyway, because he doesn't want to insult Handsome Hobo, even if the only thing the man is able to give him is something he found in the dumpster out back.

And really, a CD? WAY better than obligating Stiles to wear an old tshirt someone had been using as a rag.

Handsome Hobo clears his throat and looks pleased, in a startlingly shy way that has Stiles fighting the urge to hug the man again.  It just makes Stiles want to know his story, to find out why the man ended up on the streets.  

"So what's your story?" Stiles blurts out.

"I have a doctorate in history," Handsome Hobo replies as though that answers everything.

WOW does it ever. Stiles is really incredibly grateful he didn't get a degree in the Arts.

****

"What is that sound?" Scott asks.

"It's beautiful," Allison continues, stars in her eyes as the music filters through the living room.

Scott makes a face of general disagreement but doesn't say a word.  "Why is the window open? It’s cold in here and we can’t afford to heat the apartment, remember? We agreed we’d try to get by on the heat filtering in from the neighbours."

"Because," Stiles answers, turning up the volume.  "Handsome Hobo gave me a CD and I'm going to make sure he hears me listening to it."

"The entire neighbourhood can hear you listening to it," Scott points out as Allison sways in place.  There's a screeching sound on the CD that sounds like a stringed instrument having a run-in with a cat and a soft cursing that is only barely caught by the microphone.  “What is this?” he puts his hands over his ears like he’s at a Nickelback concert next to the speakers.

“I dunno, does D. Hale mean anything to you?”

“Oh my god,” Scott wails.  “Stiles, that’s Derek! Derek Hale. From 6B.”

“Awkward. I wonder if he can hear that I’m playing the CD he threw out.”

***

"Derek, why is your neighbour playing your awful lyre music?" asks Cora as she unwinds his scarf from her neck. "Are you writing chamber music love ballads again? Is this a cry for help?"

Derek doesn’t understand why his sisters always feel the need to drop in unannounced and eat his snacks.

"Urgh, kale chips," says Cora, her mouth twisting in a grimace at the half eaten kale on his desk. He already ate the rest of the muffins Handsome Hipster gave him.   It had been an experiment in self discipline.

"He’s playing it?" Derek’s face perks up from his research fugue state. He’s been listening to his study playlist with his headphones on all day.

"How can you not hear that?" Cora opens a window to the particular lilting melody of the bawdy ballad that he deconstructed for his master’s thesis. “Goddamn hipsters, trying to make the lyre happen.”

"The lyre is an amazing instrument," huffs Derek and preens at the fact that his neighbour is listening to it.

"It’s a trash instrument, Derek,” Cora says. Derek just glares at her. Not everyone can be a child music prodigy. She’s still sore on having to share the Christmas family concert limelight with him growing up. Sadly the violin and the lyre actually had a lot of overlap while Laura played backup on the triangle.

"I should have known something was wrong when you stopped shaving," she mutters as she turns to raid his kitchen cabinets.

Derek just smiles out towards the window where he can hear the final refrain of his stringed masterpiece.

***

"Oh my God," groans Scott underneath his pillow. "Please stop playing this."

Stiles ignores him and tries to drum out the beat with his old drum sticks.

***

Stiles nearly drops the coffee he’s holding in shock. There’s a girl talking to Handsome Hobo, she’s wearing a leather jacket and wool tights and a knitted dress that can swear he’s seen Allison and Lydia gush over. She’s getting into a cab wearing the scarf Stiles made.

It’s worse than Stiles thought. Handsome Hobo is being taken advantage of.

***

So… Handsome Hobo has a John? a Madam? a… Stiles doesn’t know, ok?  He doesn’t, but it makes him feel weird to see someone else wearing the scarf he made.  He stomps back to his apartment, aggressively knits another scarf, and keeps it on him until he runs into Handsome Hobo getting off the bus.  Stiles knows things.  He knows that sometimes homeless people ride the busline to keep warm.  The thought of it makes him cold inside.

"Here," Stiles says, handing over the scarf.  It doesn’t exactly match the rest of the knit stuff because Stiles had run out of wool, but it’s not bad either.  

"Oh, thanks… how’d you know?" the guy asks, a frown between his eyes.

Stiles gestures vaguely in a way he hopes means he doesn’t really know what the guy is talking about, he just wanted to give him ANOTHER scarf, and not in a way that means that sometimes he watches for Handsome Hobo from his window, and is halfway convinced the guy breaks into the (what should be, but Stiles KNOWS IT ISN’T) secure lobby of the apartment and sleeps on the litter of flyers beneath the mailbox.

"My sister took the last one," the guy says, all warm eyes, crinkling at the corner as he looks at Stiles.

"Your sister," Stiles repeats in a cold tone. Part of him wonders if it’s a cover story, but he doesn’t think so.  He remembers the last time the Handsome Hobo had mentioned her.

That bitch.  She was why Handsome Hobo was LIVING on the streets and selling his… Stiles wasn’t thinking too carefully about what a handsome face and smoking body could sell for these days.  Very little, he suspects.

***

Derek smiles at his neighbour. Well, not a direct neighbour. Derek has one of the two floor lofts on the sixth floor that has a spiral staircase to the seventh where the last tenant broke through the floor to link both apartments together. It’s one of the reasons Derek’s never wants to look for a closer apartment to the campus.

He had been contemplating calling Cora again to remind her to bring the scarf back for Christmas holidays, especially considering that receiving a hand-knit scarf from a hipster is probably pretty significant in the Hipster Mating Ritual hierarchy.  Cora is a notorious clothes thief, though. A few of his worn Henleys have been missing since her visit. Along with some of his comfier jeans. ("rattier, Derek, they’re falling apart," declared Cora with a frown - he’s sure Laura put her up to it. He only found one pair in the dumpster.  The rest are now half way across the country now, he's sure of it.)

The Handsome Hipster is surprisingly quiet. Usually Derek can’t get a word in edgewise before he’s gone.

"Would you like a coffee?" he offers because the last three cups have been graciously, if bizarrely, given to him by the plaid wearing neighbour. His morning lecture is canceled for midterm revisions, and Derek is awake anyway. Maybe he can finally get to know the man who’s been so generous to him.

"I couldn’t," stays the Handsome Hipster, like Derek has burned him.

Derek’s heart sinks at bit. He knows he’s not a catch and hasn’t dated since grad school but he thought the guy at least liked him enough for coffee.

***

Derek’s just getting used to remembering to bundle up in the morning when the city is hit by a sweltering heat wave.  It goes from hovering around the freezing mark to being hotter than even the warmest day of the summer, and Derek really feels it when he wakes up, the heat still on in the building, and sweat dripping from his beard.

It’s the biggest irony of his life that he’s just too hot to shave, and he just finished shoving all of his summer clothing into storage less than a week ago, and there is no way he’s going to dig everything out for what promises to be a few days of an indian summer before the temperature drops drastically again.  

So in a fit of heat fueled delirium he takes the jeans Cora tried, and failed, to throw out on him and cuts off the leg just below the knee.

He kept sniffing the air for the phantom scent of garbage every time he wore them anyway.

The lengths of the legs are uneven, but Derek’s sure no one is going to notice. He won’t be the only one out there ill prepared for the heatwave…

He’s filled with regret, ok! He knew that it was a bad idea the first moment the scissors made the first incision, but Derek is also super stubborn, and he’s going to wear his cutoffs in the abnormally warm November.

And he’s going to enjoy his coffee.

Iced.

“No,” Danny says as Derek gets to the front of the line and says his order, which is his usual order just iced.  Danny gives him a look of such severe judgement that Derek’s confused for a moment.  Iced vanilla latte is a thing - it isn’t even a weird thing.  “I’m sure this falls under no shoes, no shirt, no service.”

“What?” Derek asks, confused.  He’s wearing a shirt.  

He’s also been told he’s the EXCEPTION to that rule.

Ok, he was 22 and drunk and at a wet t-shirt contest buuuut still. The ‘no shirt’ thing isn’t something people usually call him on.

It’s been established that not all of Derek’s decisions are the best ones.

“Miguel,” Danny shakes his head, opens his mouth to speak to him and then shakes his head again.  “If I make your coffee will you promise not to drink it here?”

"What?" Derek starts.

"Please leave," Danny says.  "I’m really no one’s sassy gay friend, but I cannot, in good conscience, have you in my sight without saying something to you about your life choices."

"Oh," Derek says, looking down.

"Yes, oh," Danny echoes.

"I didn’t think anyone would notice."

"Leave now.  You have your coffee, now go." Danny looks like it’s taking some major willpower not to take Derek shopping.  Derek has seen that look before.  His entire family has given him that look from time to time.

Derek leaves, because he knows Danny has his best interest at heart, and he really, really hopes that he can get back to his apartment before anyone (else) he knows sees him.

So of course, just as he’s fleeing out the door of the Starbucks, the Handsome Hipster walks in.

****

The Handsome Hobo actually averts his eyes and shuffles off quickly when Stiles comes face to face with him on the way into the Starbucks.

"I can’t believe he had the guts to come in here," gripes Danny from the cash and Stiles can’t believe likeable Danny to be as cold hearted and cruel as Jackson.

"Hey," Stiles says with a glare. "He’s a paying customer.  So what if he’s had a few mishaps in life."

Handsome Hobo has the same rights as any one of these uppity Starbucks’ snobs.

Danny just laughs. Like it’s a joke.

"Miguel’s lucky I served him at all," says Danny.

And Stiles can’t believe it, Danny of all people!

"Well, you lost one customer today," declares Stiles before turning his back to his friend.

"What? Stiles?" Danny frowns but Stiles walks out of the coffee shop only to not see his Handsome Hobo anywhere. No, he means, ‘the’ not ‘his’.  The Handsome Hobo - he’s sure the Handsome Hobo could do better than Stiles.

***

Derek lets out a relieved breath after he’s safely back in in apartment. He can’t believe his Handsome Hipster saw him.

Maybe he’d think the look was ironic?

The look is ironic, Derek manages to convince himself.  He has a doctorate and hates the beach, wearing jorts doesn’t get more ironic than that.

***

"I had a strange run in with Stiles because of you," Danny says to him the next time he’s in Starbucks.  "I was really confused, do you know why it happened?"

"It was a mistake, ok?  Stop doing Cora’s dirty work! I won’t wear them again, I promise. I threw them out, you don’t have to worry about my sense of style."

"What?" Danny asks, his brow furrowing in confusion.

"It was one mistake!" Derek hisses, glowering at Danny.  "You sound like Uncle Peter."

"I’m just going to…" Danny gestures over to the coffee machine.  "No, you know what," Danny says when he returns with Derek’s coffee, "I don’t want to know.  I think I’ve figured out your side of it, at least, but really… just leave me out of it, ok?"

"My side of what?"

"Stiles / styles.  Enjoy your coffee, and believe me when I say your fashion taste is more than one mistake. You look like a homeless person on the best of - _Oh My God_.”

"Danny?"

"You’re going to get me fired, please leave," Danny gets out, hunched over with one arm braced against the counter. He’s shaking with laughter. Derek looks over the edge of the counter at him and then at the irate line of coffee drinkers, half of whom have identified him as the reason their coffee isn’t in their hands.

It’s a tactical retreat.

***

Derek just finishes outlining the way the way his coffee invite had been turned down to Isaac when he spots the very topic of discussion.

"That’s him," Derek nods out the windows at Starbucks as the Handsome Hipster walks by, a Harry Potter scarf (obviously hand made, with the same dropped stitch flaw most of his work possessed, not that Derek MINDS) wound around his neck about three times.  It’s not THAT cold out yet, and Derek can hardly see the guy’s face.  What he can see is giving a crude gesture towards the coffee shop, just as Isaac looks up.

Great.  

"Ah huh," Isaac says, eyes following the guy.  "Maybe he’s the type of hipster who is ANTI Starbucks."

Derek is just kind of confused.  He didn’t know there was such a creature.

"I wish I knew his name," Derek says into his coffee.

Isaac guffaws.  ”Oh man, you’re PINING.”

“No way.”

“Derek, unlike me your face just isn’t made for scarves, especially not monstrosities like that one.”

Three days later, the guy approaches him as Derek waits for Isaac to get out of the bathroom in his apartment upstairs.  For all his coffee addiction, Isaac has the tiniest bladder.  You’d think Brits would be better at holding it, what with generations of tea addiction behind them and… is that offensive? Generalizing?  Derek considers this as the guy approaches and lights up when he sees Derek.

"Look, I’m sorry," he says, giving Derek the full benefit of his bright eyes, and awww shit Derek IS pining.  Derek can’t really see the guy’s eyes because his breath has escaped from the top of his scarf from where it’s looped around his mouth (Derek KNOWS he’s pining because he’s kind of mourning the fact that the Handsome Hipster is bundled up) and is fogging up the lenses.  "I think I insulted you, and I really didn’t mean to.  Thanks for your offer, it really means a lot to me that you asked.  Like, so much, you don’t even know and it means so much more coming from you. More than I can express and I just wanted to say… HEY MY WALLET!”

Derek takes a second to catch up, because all he saw was Isaac finally getting his ass out of the building and standing behind Handsome Hipster, giving Derek encouraging expressions.

Or he needs to pee again?

But then he realizes that the Handsome Hipster is actually clutching the flap of his ironic bag that looks like the one Derek got teased for having in first grade, and that Isaac is spinning on his heel.

"Hey," Derek chides, grabbing his friend by the arm of his cardigan.  "Are we really doing this?"

"I guess not," Isaac responds, tossing the wallet to him.

"You saved me," Handsome Hipster breathes.  Derek assumes there are stars in his eyes because he still can’t see them.

But he’s PINING, he’s allowed to dream up certain liberties, ok?

***

The douchey scarf cardigan wearing mugger has already sprinted down the street but Stiles doesn’t care. Because Handsome Hobo saved him. Well, saved his wallet. But shit, his wallet has his life in it.

“Thank you,” he says heartfeltly. No wait, that’s not a word. Is it? He can’t express how deeply he’s moved. Platonically of course. Nothing untoward. Okay, maybe a little. But Stiles isn’t blind. Handsome Hobo has got it going on. Especially in jeans. The tightest ones he’s seen. Not a ratty hole to be seen actually.

Handsome Hobo looks back towards where the mugger ran off.

"I should-" he gestures. And Stiles nods with understanding. Honour among thieves. He probably knows him. Or maybe, dare Stiles hope, off to defend his honour?

He’s gone before Stiles comes to his sense to invite him up to his apartment for coffee.

***

"His name is Stiles," Isaac says, winded and wheezing because his lungs are delicate to temperatures beneath the freezing point.  Derek tries not to judge too harshly.

"Stiles?" Derek echoes, and the name is already committed to memory.  "You saw his ID?"

"I didn’t have to," Isaac wheezes, and Derek realizes the asshole is laughing at him, not having lung problems, at the same time Isaac continues with.  "The wallet is hand embroidered Property of Stiles. Badly."  Isaac doubles over, obviously laughing again.  "You know how to pick them."

Derek’s frown settles into a scowl, even though his heart feels pleased.  The same kind of pleased it felt when Stiles hugged him.

***

Stiles throws his bag on the floor when he enters the small apartment he shares with his bestie.   Scott’s sitting in their one duct tape free chair highlighting a used textbook with wilful abandon.

"The Handsome Hobo saved me from being mugged, Scott!" Stiles announces. That kind of heroism should be shared.  “I have to do something to help him. I knit him a scarf, and a hat, and mitts, and another scarf because his sister… that bitch… stole his first one and then didn’t give him a place to live.   I spent all day at work thinking about it!  And I think I have the solution.  I need to find him a place to live.  And finish knitting these socks.”

"Stiles, that’s Derek Hale, he lives in 6B," Scott says nonplussed as he highlights another section of the book.  “So you don’t misunderstand me: dark hair, green eyes, wears a ratty grey cable-knit sweater half the time?  Derek Hale.”

The warm feeling in Stiles body turns to frigid ice.

"Wait, what?”

***

He’s settled into his pajamas, the nice silk set with the monogram his sister gave him because she thought he should own at least one nice thing, and Derek wasn’t going to not wear the most comfortable pajamas he’d ever put on just to spite her, when a knock came at the door.

He opens it, and is really, really happy to see Stiles.  Stiles.  He knows Stiles’ name now, and he can’t help the smile that crosses his face until he sees Stiles take him in and his mouth turn down.

"You’re something," Stiles snarls, hanging onto the door frame as though he’s physically restraining himself from coming closer.

"Excuse me?"

"I thought for a second that maybe business had really picked up, but Scott says you’ve been here since before we moved in.  That you helped him drag up our television when I was running late.  I THOUGHT YOU WERE HOMELESS,” Stiles wails, throwing his hand over his face.  ”DO YOU KNOW HOW EMBARRASSING THAT IS?”

Derek has a moment of being absolutely speechless.

Fuck.  

He should never have worn those jorts.

"I was in the process of sweet talking my boss into giving you a job interview! I knit you these socks!" Stiles continues, brandishing tubes that did not look to have a curved heel.  "I sometimes make a carafe of hot chocolate and bring it down to the lobby because I thought you could use something sweet."

"I…uhm," Derek manages.

"And then I wait for an hour just to make sure you’re not going to show up once the bus stops running.  And now I find out you own silk pajamas and live in the penthouse.  I’m supposed to be saving this story from being The Little Match Girl, not turning it into Daddy Warbucks."

"That doesn’t make sense," Derek manages to say, and then cringes because of all the things for him to respond to, of course it’s the wrong one.  "I didn’t… if I knew you were thinking that, I would have told you the truth," he settles on, feeling so confused and more than a little insulted.  Dammit, his sisters were right.  He might have to let them take him shopping. “I didn’t deliberately…”

Stiles cuts him off with a wounded sound, his hand actually slicing through the air.  "I can't stand here and stare at your face.  I don't know whether to be angry or embarrassed."

Derek shrugs hopelessly, because he doesn't know either.  "I thought you were courting me," he mutters, shuffling his feet awkwardly.

Stiles seems to focus on the movement, and then his head whips up to stare at Derek's face.  "Courting..." he echoes with a small smile.  "Kind of.  In a way, I guess.  You wore the mittens and the scarf and the hat anyway.  You can afford better, but you still wore them."

Derek nods, because he had.  "I think I really need to take you out for coffee.  Will you let me, now?"  Now that Stiles knows he can afford coffee.  Wow, that suddenly makes sense.

"I need... I'm going to go reassess my life," Stiles says, pointing his thumb over his shoulder.

***

"Okay," Stiles says when they meet the next evening in front of the mailboxes.  

"Okay," Derek repeats, holding open the front door.  "Okay," he says again with a smile and a sense of relief.  "Coffee, then?"

***

Danny grinning, "Oh, Stiles, you finally met Miguel," as he rings up their order at Starbucks is just the icing on the misunderstanding cupcake of their love lives.

end.

**Works inspired by this one:**

  * [[Fanart] Handsome Hobo](https://archiveofourown.org/works/2876255) by [Belayday](https://archiveofourown.org/users/Belayday/pseuds/Belayday)
  * [[Podfic] Handsome Hobo](https://archiveofourown.org/works/3282287) by [Belayday](https://archiveofourown.org/users/Belayday/pseuds/Belayday), [relenafanel](https://archiveofourown.org/users/relenafanel/pseuds/relenafanel), [Swing Set in December (swing_set13)](https://archiveofourown.org/users/swing_set13/pseuds/Swing%20Set%20in%20December)




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